Yes, it is possible to sell your HDB flat after meeting the Minimum Occupation Period (MOP) and upgrade to a condo. However, if you purchase a second house, you’ll first have to pay the Additional Buyer's Stamp Duty (ABSD) as usual (within 14 days of the date of purchase). You can apply for a remission if you sell your first home within six months of buying the second one.
If the second property is under development (e.g., a new launch condo), you must sell your first house within six months of the second property getting its Temporary Occupation Permit (TOP) or Certificate of Statutory Completion (CSC), whichever is earlier.
Good luck with your property upgrade!